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Volumn 127, Issue 29, 2005, Pages 10243-10249

Can polarization of triple bond in tolanes be deduced from 13C NMR shifts? Re-evaluation of factors affecting regiochemistry of the palladium-catalyzed hydrostannation of alkynes

Author keywords

[No Author keywords available]

Indexed keywords

ANISOTROPY; CATALYSIS; ISOMERS; PALLADIUM; POLARIZATION;

EID: 22944440095     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja051274v     Document Type: Article
Times cited : (63)

References (36)
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    • note
    • 13C HMQC and HMBC NMR spectroscopy for each of these compounds. See Supporting Information for details.
  • 23
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    • Wavefunction, Inc.; Irvine, CA
    • Spartan 02; Wavefunction, Inc.; Irvine, CA, 2002.
    • (2002) Spartan 02
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    • and references cited therein
    • (b) Pulay, P.; Bofill, J. M. Chem. Phys. Lett. 1989, 156, 501 and references cited therein.
    • (1989) Chem. Phys. Lett. , vol.156 , pp. 501
    • Pulay, P.1    Bofill, J.M.2
  • 30
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    • Gaussian, Inc., Pittsburgh, PA
    • Gaussian 03, revision B.05. Gaussian, Inc., Pittsburgh, PA, 2003.
    • (2003) Gaussian 03, Revision B.05.
  • 31
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    • note
    • 11
  • 32
    • 33444463787 scopus 로고    scopus 로고
    • note
    • zz)/3. Finally, current density surfaces were mapped with shielding densities, using GaussView 3.09W, Gaussian Inc, Pittsburgh, PA.
  • 33
    • 0005570861 scopus 로고    scopus 로고
    • Magnetic shielding phenomena may be viewed as a result of interaction between an induced magnetic field and the permanent magnetic moment of a given nucleus with a nonzero magnetic moment. Such a nucleus is referred here and below as a probe nucleus. For discussion, see: Wolinsky, K. J. Chem. Phys. 1997, 106, 6061.
    • (1997) J. Chem. Phys. , vol.106 , pp. 6061
    • Wolinsky, K.1
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    • note
    • 9
  • 36
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    • Although the exact mechanism of the Pd-catalyzed hydrostannation is still unknown, it is generally believed that it proceeds via an initial hydropalladation rather than a palladastannation step (see ref 10). We propose that, in this case, nonconcerted migratory insertion results in hydride approaching and adding to a triple bond faster than palladium. Consequently, palladium adds last and to a more hindered site, overall affording α-stannylated stilbenes. For a similar steric effect governing regiochemistry of carbopalladation in the Heck reaction, see: Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
    • (2000) Chem. Rev. , vol.100 , pp. 3009
    • Beletskaya, I.P.1    Cheprakov, A.V.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.